Swirl Pt. 06

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Pleasure and Pain.
5.2k words
4.7
11.8k
6

Part 10 of the 11 part series

Updated 09/21/2023
Created 10/23/2017
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Every single chance Tori and I got, we went for a drive. It was definitely our thing. We loved it. We loved being together like that. We visited wineries. Made runs on various river roads through cute little old towns. Visited lots of parks. Most of all, we just enjoyed each other and grew deeper in our relationship.

Well, as our relationship evolved, so did our drives, and we progressed to our first road trip. We decided to make a weekend trip to Chicago. Tori had never been. It had been awhile for me. Chicago is one of my favorite places to visit. I absolutely love Chicago and couldn't wait to share some of my favorite places with her.

Friday morning we packed up a few things and headed out onto the highway. Anxious for what lay ahead. Tori was her usual self excitedly taking command of the music. Singing, laughing and poking fun at me.

"I like your haircut Daddy."

"Thank you. Do you think it's too short on top?"

"No, why?"

"I don't know. Can you get a good grip on it?"

Tori reached up and tried to grabbed the top of my hair, but wasn't able to get a good grip.

"No, but what the fuck for?"

"So you can pull me deeper into your pussy. I guess no oral sex for you until it grows out. Lucky for you my hair grows fast."

Tori laughed, " Hell No! I'm gonna grab you by the ears and pull you deep into this pussy. You crazy."

"You and that pussy make me crazy Tori."

We went on like this all afternoon until we pulled into downtown Chicago in the later that day. Fighting traffic. I had decided to splurge and booked a room at the Four Season's just off of Michigan Avenue. I got a good deal and wanted to pamper her. Tori loved the view of the downtown area, excited to begin exploring.

"What are we going to do first Daddy?"

"Let's go across the street to Water Tower Place and do a little shopping and I would like to get some popcorn from Garrett's. Then later tonight I want to take you someplace really different for a late night meal."

And that's just what we did. We leisurely walked around. I bought Tori a cute dress at Armani Exchange as we laughed and fooled around a little in the dressing rooms. We capped off our little shopping adventure with grabbing a little bite to eat and picking up some Chicago Mix popcorn from Garrett's. We took a short stroll down Michigan Avenue and back north again on Rush Street and hit some bars getting nice and lit.

As it got pretty late we caught a ride to my little surprise, Wiener's Circle. I had warned Tori that the Wiener's Circle was particularly known for their special kind of hospitality. Tori was anxious to join in. If you are not familiar with the Wiener's Circle, check them out on You Tube to see for yourself.

The Wiener's Circle wasn't too crowded. But, as usual it was rowdy.

As we got close to the counter holding hands ready to order, the girl yelled out "Aww Shit look at you two fuckers. Bitch, you really with this white boy?"

"Fuck yes," Tori shot back.

"Hell no. He rich or something?"

"No. But he rich with the dick."

"Bullshit. Ain't no way that white boy packing."

Very loudly and proudly Tori shot back, "packing nine fucking inches. Now get us a couple Char dogs and fries you jealous cunt!"

Of course I didn't say a damn word. Just stood there enjoying the atmosphere. Tori joking around with the other drunk patrons.

"That's right. Nine nine nine nine nine. All mine mine mine mine mine," she laughed out loud.

We had a great time eating, laughing and watching the on going hostile humor between the customers and employees.

"Wrigley Field is just up the street a bit. It's my favorite place on the planet, especially when the Cubs are playing the Cardinals. We'll have to come back up when they are playing. There is nothing else like it. The atmosphere is electric. It's one big party," I said.

"You know I'm not that into sports, but If I can get my drunk on and party with you I'm game," Tori replied.

"Cool. Another road trip then on the books," I laughed. "What do you say we head on back and crash."

On the ride back to the hotel, Tori was constantly rubbing my cock through my pants singing and laughing, "nine nine nine nine nine. All mine mine mine mine mine."

Once inside the room, I commanded Tori, "Get your clothes off now!"

Tori did as told. "What are you going to do to me Daddy?"

"You were flaunting me to everyone at Wiener's Circle, so I thought, we would give downtown a show."

"Oh shit."

"Now stand over by the window facing the city. Hands on the glass. Show everyone how sexy you are and how lucky I am."

"It's so beautiful Daddy."

I removed my pants and underwear. Got on my knees behind her. Pulled open her ass and began tonguing her asshole.

"Oh Fuck the feels good and nasty Daddy. Lick it. Stick you tongue in my ass. Yes."

I alternated between her asshole and her pussy. Taking my time. Enjoying every second of her beautiful responsive body. Licking up the juices from her pussy. Sucking her clit in and out of my mouth. Back to rimming her ass. Tori grinding more forcefully into my face. At one point she reached back and grabbed my hair and laughed as she pulled me deeper into her ass, "Yep, hair's long enough."

I started to pick up the intensity wanting her to come.

"Baby girl can you come for me and all of Chicago."

"Yes Daddy. I want them to watch me come."

"That's my good little dirty girl."

I attacked her pussy pushing her to give me that nut. We were working together now. Faster rhythm and intensity. Closer and closer she got. I sunk a finger into her ass that pushed her over the edge and she shook through an intense orgasm. Her pussy leaking as I tried to keep up licking it all.

"Now give me my nine Daddy!"

I was already rock hard and didn't waste any time. I stood and quickly as possible buried all of my cock into her and held still.

"Oh shit that nine is all mine. Shit Daddy I was getting so horny making sure they all knew that your big dick was mine. Jealous bitches. Now give it to me ."

"You dirty bitch. Take my cock while everyone watches"

"Fuck Yes Daddy! Fuck me hard."

No time for romance; just plain urgent fucking.

"You like showing off don't you baby girl?"

"Yes Daddy. But, I like fucking you more," she said.

"I'm getting ready to come and I want you to show everyone more."

"What do you mean Daddy?"

"On your knees,: I barked.

"Be my little porn star and take my come."

"Give it to me Daddy. Come on my face."

"Fuck, I've always wanted to do this. Here it comes. Ugh."

I stood over Tori jerking my cock excitedly as I shot a number of ropes of come onto her face and into her short cropped red hair.

"Fuck, it's so hot. Keep giving it to me. Mmmm yes, in my mouth."

I finally let up. Tori's face was covered.

"Turn to face the window and your audience baby."

"Jealous Mother Fuckers. Thank you Daddy."

"No, thank you baby girl."

We didn't rush to cover up, or even check to see if anyone was really peeping in on us. We were just comfortable to rest on the sofa. I retrieved a washcloth and cleaned Tori up. We took a shower together and settled into bed. Watching TV. Cuddling and falling fast asleep.

The next morning we ate breakfast and hit Michigan Avenue. Stopping here and there. Took our time in Neiman-Marcus. Tried to pick out everything we would want to have in our future country home from Crate & Barrel. All we need to do now is win the lottery to make that dream happen.

We made our way south along Michigan Avenue, across the Chicago River to one of my favorite places, The Art Institute.

I felt like a billion dollars walking around the Art Institute holding hands with the most beautiful thing in there. I took her to see my absolute favorite painting.

"Tori, in this next room is my favorite painting. Let me know what you think of it."

We walked into the adjoining room and Tori stopped dead in her tracks.

"You serious? This is that Ferris Bueller painting."

"I fell in love with this painting long before that movie came out. It's incredible."

"It's different in person. It's big."

"Now get up close and look at the points and how it's done."

We got up as close as we could and Tori marveled at the technique and time it must have taken to create this large masterpiece.

"It's much more impressive in person. Oh my God, It's beautiful."

We continued on hand in hand. Tori would get excited when she got to see works of art the she was familiar with. American Gothic and Nighthawks to name a couple.

"Before we go, there are a couple more of my favorites that I want to show you. They are not beautiful in their nature but they are beautiful in their detail and execution," I said.

I took Tori to see a couple of paintings by Chicago artist Ivan Albright.

"This one is commonly called 'The Door'. How bout we have this as one of our doors to our future country home."

"Oh my God. I don't know how to describe it. The absolute decay is freaky. Fucking cool. Dark. Ugly. Creepy. Really cool."

"I could stare at this all day. But here let me show you the last one of Dorian Gray. The old dude like me," I laughed.

"He is fucking ugly. Not like you Daddy. He is ugly and decayed just like the door painting. Sick and twisted, but, really cool."

"This was painted for a movie back in the day. We'll watch it some day.

We left the Art Institute and walked around Millennium Park for a bit. Then caught a ride over to Shed Aquarium. I've never been into fish or seafood in anyway and wasn't that interested, but, Tori really wanted to see it and got a big kick out of it.

"Daddy, we have done a lot of walking today. I'm getting tired and hungry as fuck. I want a big ass steak."

"I know just the place."

We then caught a ride up to Lawry's on Ontario.

I watched Tori's face light up when the overpowering smell of Prime Rib hit her in the face as we walked through the front door.

"Oh My God! Get me a table now," she laughed!

We were a pretty funny sight for the kind of old school crowd in the restaurant. Older white guy with a beautiful young black woman. Both devouring our Prime Ribs like hungry wolves.

On the walk back to the hotel we stopped at a couple of bars and had a few drinks loosening up and then back to the room.

Tori went into the restroom to freshen up while I crashed on the couch; not sure if I had enough energy for what I had planned next. But, Love and Desire always win out as I wanted to help fulfill one of Tori's needs.

"Tori, come over here."

Tori came over to the sofa I was sitting on with a curious look on her face, as she tried to determine the serious tone in my voice.

"Stand in front of me. Now, take your clothes off."

"Yes sir," she said softly.

She slowly began taking off her clothes. Neither one of us saying anything. Just staring into each others eyes.

"Now take out your nipple piercings."

Once completely naked, I picked up her clothes; folded them and started to take them to the bedroom.

"Stay here Beautiful."

"Yes Daddy."

I returned back to the sofa with a package. I reached in and pulled out the blindfold. Next, the zip ties, and then the riding crop. Tori bit her lip.

"Do you remember these?"

"Yes Daddy. I have been waiting for you to use them on me. Use me Daddy."

"So just as a reminder, Red means stop, Yellow means to slow up and Green means to continue. Understood?"

"Yes sir."

"I have some other surprises that I will share as we go along. Would you like to see one of them now?"

"Yes please."

I reached into the package and pulled out a blue crystal butt plug.

"Your favorite color. What do you think I'm going to do with this? Tell me?"

"You're going to fuck my ass with it."

"Yes I am. Would you like me to fuck your ass baby girl?"

"Yes, Daddy. My ass belongs to you. Punish it and fuck it hard."

"I intend to baby girl. Now open your mouth."

I inserted the butt plug into her mouth and picked up the riding crop. I brushed the riding crop around her breasts. Toying her nipples with the leather flap on the end of the crop. I moved around behind Tori, lightly tracing the lines of her back with the crop. Moving down to her ass and gently probing between her beautiful cheeks.

I moved back around to her front. Lightly tapping her nipples with the end of the crop. Running it down her stomach and into the lips of her pussy as she groaned. I pulled back to notice her wetness now on the leather flap. I put it to my lips and licked her sweetness.

"I think someone is a little excited?"

Tori could only moan her approval.

"You are so beautiful and delicious baby girl."

I moved the crop back to tracing circles around her breasts and nipples. I pulled back and gave her left nipple a fairly hard swat. She groaned loudly and jerked back.

"Come here baby girl."

As she approached, I quickly gave her right nipple an equally hard swat. Once again she moaned against her butt plug and jerked backward.

"Stay put," I demanded.

I pulled her head back by the hair and began swatting her breasts and nipples relentlessly. Tears filled her fearful eyes as I continued to redden her breasts with marks from the riding crop. She spit out the butt plug and started breathing heavy. I leaned down and began sucking on each of her stiff reddened nipples.

"Oh Fuck Yes Daddy!"

I gently bit down on each nipple causing her to yell out. With my left hand I reached down into her pussy. She was soaking wet. I removed my hand and coated her nipples with her wetness and began sucking them hard into my mouth again.

"You are so fucking wet baby girl."

"Daddy you got me so fucking hot. Use me. Abuse me," she said as tears streamed down her face.

"Take off my pants baby girl."

Tori proceeded to unlace my shoes and take them off. She then unbuckled my belt and undid my pants pulling them to the floor. I kicked my legs and feet free and Tori placed the pants on the sofa. She then lowered my boxer briefs freeing my hardening cock.

"Now I want you to take my belt from my pants and give it to me," I ordered.

Tori did as instructed. I took the belt and wrapped it around her neck and through the buckle creating a leash. I squeezed it tight to definitely make her feel it. She let out an involuntary moan.

"Kneel down in front of me and stroke my cock little one."

"Yes sir."

Tori kneeled down and lovingly grasped my cock in both hands and began jerking me. Occasionally bringing her right hand down to massage my balls. She leaned forward to take the fat head into her mouth swirling her tongue around the head filling her mouth all while stroking the shaft back and forth and pulling on my balls.

"I love watching you stroke my cock little one."

"I love your cock Daddy. My cock."

"Keep stroking your cock little one."

I could watch her work my cock for hours, but, I had other plans.

I pulled Tori up by the leash. I backed away and reached into my package and took out some nipple clamps. With my hard wet cock poking her in the stomach I fastened the clamps to each of her nipples causing her to yell as they gripped tight.

"Now hold out your hands. Wrists together."

I took one of the zip ties and securely zipped her wrists together. Lastly, I put the blindfold over her eyes and left her alone for a few minutes.

"Daddy, where are you"?

"I'm right here baby girl'?

What are you doing"?

"I'm stroking my cock looking at your beautiful body and you red enflamed tits."

"They really hurt Daddy."

"Do you want to stop?"

"No sir. Use me."

With that, I jerked the belt leash tight and started leading her into the bedroom. I led her to the foot of the poster bed. I took another zip tie and looped it through the other and fastened it tightly around the post of the bed.

I went back to the sofa and retrieved the riding crop, butt plug and returned to the bedroom picking up some other surprises for her.

I put on a playlist of music that was a soundtrack for our relationship. "Pillow Talk" by ZAYNE. "Planez" by Jerimih. "Worth it" by The Weeknd.

"Present your ass for me baby girl."

"Yes sir," as she bent over slightly.

I traced the end of the crop around each cheek and down between the crack over her rosebud. Then down between her legs into the lips of her pussy.

"Yesssss Daddy."

I pulled out the crop and swatted her ass with a quick hit.

"Ohhh FUCK!" Tori jerked and yelled.

"That left a quick red mark. Do you want more?"

"Yes sir," she whimpered.

I followed that with two quick strikes across her ass causing her to yell. I moved forward and rubbed my cock against her ass leaving trails of pre-cum along the fresh red marks on her ass.

"Oh Fuck Daddy," she breathed as she gathered herself.

"More?"

"Yes sir."

I lit into her ass with consecutive hits causing her to scream out. I leaned down and kissed each red mark on her ass. Pulled her ass apart and tongued her asshole.

"Oh Shit Daddy Yes!"

I went lower to her pussy. It was leaking her excitement down onto her legs. I had never seen her pussy that wet before. I enjoyed licking her clean as I rubbed her enflamed ass. Tori started grinding her pussy into my mouth.

"Yes Daddy Yes!"

I stood and went to retrieve some lube and the butt plug. I wetted my middle finger with lube and reached in to tease her rosebud.

I leaned into her and whispered, "Its time for your favorite color baby girl."

I eased my finger into her ass as Tori took in a quick grasp of air. I worked my finger slowly in and out of her ass as she relaxed and began opening herself up for me. I bit her earlobe and flicked a nipple clamp with my other hand causing her to tense up as I increased my penetration of her ass and adding another finger to stretch her open.

"Are you ready for the blue?"

"Yes Daddy."

I withdrew my fingers. Lubed the butt plug and teased her rosebud with it.

"Relax baby girl. Relax your ass for Daddy."

I slowly and carefully added pressure to gently insert the plug. I loved watching Tori's body react to the invading plug. She was breathing deeply trying to relax as the plug was stretching her ass open. One last little push and it slipped in to the base.

"Good girl. You look so beautiful. How does it feel."

"Shit Daddy I feel so full."

"Does it hurt little one?"

"No sir."

I began tapping the end of the plug first with my hard cock and then with the end of the riding crop.

"I love seeing you like this," I said.

"I love making you happy Daddy," she replied.

"And I love fulfilling your needs."

"You do Daddy. Please use me."

I paused for awhile to admire her. To watch her adjust to the new feelings in her ass. I took a few moments to prepare her next surprise. Then, when she wasn't expecting it, I switched her ass with five hard whips of the crop.

"Oh Fuck," she screamed as she fell to her knees and was panting heavily.

Perfect. Exactly where I wanted her. I moved into position. I laid on my back, moved her legs apart and wiggled between her legs looking up at her pussy.

"Lower your pussy onto my mouth baby girl."

Her pussy was soaked. I took my time. Kissing and nibbling her inner thighs. Her wet lips waiting and opening for me. Her clit hard was exposed begging for my attention. Tori moaned in anticipation. I began sticking my tongue into her cunt as her excitement flowed into my mouth.

"YES," she breathed as her pained ass was being compensated by my pleasuring tongue.

My God I loved this girls wet and responsive pussy. I drilled her pussy with my tongue and pulled out licking all around her lips. Then sucking her lips into my mouth. Followed my more digging my tongue as deep into her pussy as I could.

"Eat me Daddy. Eat that pussy. That's it, eat your pussy."

The intensity was building as I paused to move to her clit and reached with my hand to her next surprise. I grabbed my strategically placed Hitachi wand and turned it on high.

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